US6855327B1 - Pesticide dispersant - Google Patents
Pesticide dispersant Download PDFInfo
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- US6855327B1 US6855327B1 US09/334,366 US33436699A US6855327B1 US 6855327 B1 US6855327 B1 US 6855327B1 US 33436699 A US33436699 A US 33436699A US 6855327 B1 US6855327 B1 US 6855327B1
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- United States
- Prior art keywords
- composite
- alkyl polyglycoside
- carbon atoms
- dispersant
- alkyl
- Prior art date
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 55
- 239000000575 pesticide Substances 0.000 title claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 239000002131 composite material Substances 0.000 claims abstract description 41
- 125000000129 anionic group Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229920001732 Lignosulfonate Polymers 0.000 claims description 22
- 235000019357 lignosulphonate Nutrition 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims 4
- 125000000837 carbohydrate group Chemical group 0.000 claims 3
- 239000002280 amphoteric surfactant Substances 0.000 claims 2
- 239000003093 cationic surfactant Substances 0.000 claims 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical group C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 claims 2
- 239000002736 nonionic surfactant Substances 0.000 claims 2
- 238000009472 formulation Methods 0.000 abstract description 23
- 239000004562 water dispersible granule Substances 0.000 abstract description 20
- 239000000843 powder Substances 0.000 abstract description 19
- 239000007788 liquid Substances 0.000 abstract description 18
- 230000032683 aging Effects 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 4
- 239000007900 aqueous suspension Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000012141 concentrate Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000008187 granular material Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- 229920005610 lignin Polymers 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000001694 spray drying Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 6
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000003090 pesticide formulation Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 239000005747 Chlorothalonil Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- -1 alkyl polysaccharide Chemical class 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical class C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000012978 lignocellulosic material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010338 mechanical breakdown Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000004537 pulping Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229920005611 kraft lignin Polymers 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/56—Glucosides; Mucilage; Saponins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/12—Sulfonates of aromatic or alkylated aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/50—Derivatives of lignin
Definitions
- WDG Water-dispersible granule
- Dispersible granular pesticide formulations are typically prepared by blending premilled, water-insoluble, active ingredient, dispersing agents, disintegrating agent and wetting agents in an aqueous suspension. The aqueous mix is extruded to form granules which are then dried to yield the final product.
- a dispersible granule herbicide composition designed for dispersion in a liquid carrier should ideally have a high content of active material, should be resistant to mechanical breakdown into a dust (attrition) should be readily dispersible in the carrier and should then form a dispersion which is as stable as possible, requiring a minimum of subsequent agitation to maintain homogeneity.
- the present invention relates to liquid or granular dispersing agents for use in water-dispersible granule (WDG) or suspension concentrate agricultural chemical formulations which are composite substances comprised of an alkyl polyglycoside and a polymeric anionic dispersant.
- WDG water-dispersible granule
- the granular composite dispersing agents are made by drying together aqueous mixtures of alkyl polyglycosides and dispersing agents to form a dry, powdered product providing significant advantages over conventional wetting and dispersing agents added individually to pesticide formulations.
- the granular composite dispersing agents according to the invention which can be used in granular or liquid-suspension agricultural chemical formulations, exhibit outstanding attrition resistance, excellent dispersional stability after accelerated aging and low moisture content when made into a paste.
- the composite dispersing agents are useful as primary dispersants in dry agricultural formulations (wettable powders and water-dispersible granules) and in aqueous suspension concentrates.
- liquid composites which are comprised of an alkyl polyglycoside and a polymeric anionic dispersant.
- APS alkyl polysaccharide which is a generic term for an alkyl polyglycoside.
- the polymeric anionic dispersant that can be used in this invention is any polymeric dispersant material having multiple anionic groups and which is capable of forming a composite with an alkyl polyglycoside.
- Such polymeric anionic substances include, but are not limited to, sulfonated lignins, sulfonated naphthalene-formaldehyde condensates, and sulfonated polystyrenes. These compounds are described in U.S. Pat. No. 4,936,901, the entire contents of which are incorporated herein by reference.
- lignosulfonates Sulfonated lignins, which are also referred to as lignosulfonates, are described in U.S. Pat. No. 3,986,979, the entire contents of which are incorporated herein by reference.
- One of the main sources of lignins is the paper and pulp industry where lignocellulosic materials such as wood, straw, corn stalks, bagasse, and the like are processed to separate the cellulose or pulp from the lignin.
- lignin When lignin is obtained from the kraft or sulfate pulping processes, it must be sulfonated before use as a dispersing agent.
- the lignin products obtained in an alkaline or neutral process of digestion of lignocellulosic materials may be readily sulfonated by reacting with a bisulfite or sulfite.
- lignin is made soluble by sulfonation and thus separated from the cellulose by dissolving in the spent liquor and is present in this liquor as a lignosulfonate.
- Any of the above-described sulfonated lignin materials may be used to produce the dispersing agent of the present invention.
- the degree of refining to which these sulfonated lignin materials are subjected, will depend on the quality of product desired and upon the economic factors involved. That is, refining to some extent will improve the properties of the final processed product, but the degree of improvement will not always be economically justifiable.
- sulfonated lignins from all sources are contemplated, the sulfonated lignins made from alkali lignin are preferred. Particularly preferred are the alkali metal salts of alkali lignin, particularly sodium sulfonated lignin. Although sodium sulfonated lignin is preferred, chemically modified sulfonated lignins may be used.
- lignins are commercially available from, for example, Westvaco under the trademark names REAX®, POLYFON®, and KRAFTSPERSE®, or from Lignotech USA under the trademark names BORRESPERSE®, ULTRAZINE®, UFOXANE®, MARASPERSE®, and DIWATEX®, or from Witco under the trademark name MORWET® D425.
- the dry powder or granular composite compositions according to the invention can be made by mixing the components in solution together and drying.
- the process for making the composites comprises mixing aqueous polymeric anionic dispersants and alkyl polyglycosides together at a temperature of from about 165° F. to about 185° F. primarily to adjust viscosity control of the feedstock to maximize the uniformity of the spray pattern.
- the mixture is then typically allowed to stand for a time sufficient to assure complete dissolution of the alkyl polyglycoside in the solution.
- Any number of conventional drying methods may be used. For instance, spray drying, force air drying, oven drying, drum drying, and freeze drying, with spray drying being preferred.
- Spray drying is preferred and the parameters necessary are well known to those skilled in the art, however, particularly successful products may be spray dried at air inlet temperatures of from 200° to 900° F. and outlet air temperatures of between 1550 and 400° F.
- the aqueous mixture of wetting and dispersing agent is normally diluted and/or heated to an easily handled viscosity prior to spray drying, i.e., 30-45% solids content.
- the ratio of alkyl polyglycoside to the polymeric anionic dispersant can be any ratio required and is dependent upon the particular pesticide contemplated and whether the composite will be in the dry powder form or the liquid form.
- the weight ratio (on a dry solids basis) of alkyl polyglycoside to polymeric anionic dispersant can be from about 1:9 to about 9:11 and is most preferably from about 1:4 to about 7:13 in the case of the dry powder form. This corresponds to a weight percentage of alkyl polyglycoside of from about 10% to about 45% in the preferred embodiment and from about 20% to about 35% in the most preferred embodiment.
- a particularly preferred composition is comprised of an alkyl polyglycoside and a sulfonated lignin in a weight ratio of alkyl polyglycoside to sulfonated lignin of about 1:3.
- the upper limit of 45% by weight of alkyl polyglycoside is used in making dry powder composites according to the invention wherein the polymeric anionic dispersant is sulfonated lignin.
- Greater amounts of alkyl polyglycoside can interfere in the efficient manufacture of such dry powder composites in the drying operations, particularly in spray drying.
- any ratio of alkyl polyglycoside to the water-soluble sulfonated lignin can be used as desired and is dependent upon the particular pesticide contemplated.
- the amount of alkyl polyglycoside may exceed 45% by weight of the composite.
- the alkyl polyglycosides which can be used in the invention have the formula I R 1 O(R 2 O) b (Z) n I wherein R 1 is a monovalent organic radical having from about 6 to about 30 carbon atoms; R 2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6.
- Preferred alkyl polyglycosides which can be used in the compositions according to the invention have the formula I wherein Z is a glucose residue and b is zero.
- alkyl polyglycosides are commercially available, for example, as APG®, GLUCOPON®, PLANTAREN® or AGRIMUL® surfactants from Henkel Corporation, Ambler, Pa., 19002.
- surfactants include but are not limited to:
- alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula I as described in U.S. Pat. Nos. 5,266,690 and 5,449,763, the entire contents of both of which are incorporated herein by reference.
- Extruded WDGs can be prepared on a Benchtop Granulator by Luwa using a 0.8 mm screen and setting the motor speed to about mid-scale, with small adjustments made to compensate for variations in paste rheology, using slower speeds for thicker pastes.
- Pan-granulated WDGs can be prepared using a 15-inch diameter rotating pan. The precise conditions required to produce the granules by either method can be determined for each combination of pesticide, dispersant, and other formulation components to minimize the proportion of oversize and undersize material. This can be done readily by one skilled in the art by visual observation of granule sizes.
- the composites according to the invention can be used in any type of agricultural formulation examples of which include, but are not limited to, those containing such biologically active substances as insecticides, nematocides, fungicides, miticides, herbicides, and growth regulators such as those described in U.S. Pat. No. 5,559,078.
- the composites according to the invention are used as a dispersant in a pesticide formulation in an amount effective to emulsify the biologically active ingredient.
- the weight percentage (on a dry solids basis) of the composites according to the invention in pesticide formulations can be from about 2% to about 99% and is preferably from about 4% to about 16%.
- the formulations can contain other surfactants including nonionics, anionics, cationics, amphoterics and combinations thereof as well as inert fillers and the like.
- the composites according to the invention When used in WDG formulations, the composites according to the invention impart superior attrition resistance while achieving good disintegration rates, maintain excellent dispersional stability after accelerated aging, allow the production of granules with higher bulk densities, which promotes free flow of the final granulated products and, in many cases, reduces the moisture content in extrusion paste.
- Formulations prepared with the dry composite dispersant system typically show enhanced performance when compared with otherwise equivalent formulations made by adding the alkyl polyglycoside and polymeric anionic dispersants as separate components.
- the dry powder form of the composite according to the invention provides a water-free surfactant that facilitates dry blending and grinding to make wettable powders and WDG premixes.
- the liquid dispersant form of the composite according to the invention can be added to WDG premixes or liquid formulations containing insoluble suspended solids (including formulation types known as aqueous flowables, suspension concentrates, or suspo-emulsions).
- a blend was prepared by mixing 300 g AGRIMUL® PG 2069 (as a liquid containing 50% solids in water) at 40° C. with 700 g REAX® 100M (as a liquid containing 40% water) at 40° C. and stirring manually for 2 minutes to attain a homogeneous mixture. Over the next 3 days, the mixture was left undisturbed and was allowed to equilibrate to ambient temperature. During this time, the mixture remained homogeneous and did not show evidence of any chemical reaction or physical separation. The blend was spray-dried according to the conditions set forth in Example 1 of U.S. Pat. No. 3,986,979. The resulting solid was a free-flowing powder that dissolved completely in water at 18° C.
- a blend was prepared by adding 7.8 Kg AGRIMUL® PG 2076 (as a liquid containing 60% solids in water) at 35° C. with 42.2 Kg REAX® 85A (as a liquid containing 26% solids in water) at 35° C. and stirring manually for 2 minutes to attain a homogeneous mixture. Sufficient concentrated sulfuric acid was then added while stirring so as to adjust the pH to 8.5 and the mixture was allowed to equilibrate to ambient temperature for 2 days. The liquid mixture was spray dried to yield a free flowing powder that dissolved completely in water at 21° C.
- Example 2 The procedure of Example 2 was repeated except that 11.1 Kg AGRIMUL® PG 2069 and 38.9 Kg REAX® 88B were used. This mixture was acidified to pH 8.5 by adding sulfuric acid. The spray-dried solid was observed to flow freely and dissolved completely in water at 21° C.
- a set of wettable powders were prepared according to the following procedure to evaluate the effect of different dispersants (a-d) in a prototypical formulation. For each formulation, the four components were pre-blended manually and then the pre-blend was passed through a 4-inch air mill to produce a wettable powder.
- Chlorothalonil (95%) 8.0% Dispersant (see table below) 1.0% SELLOGEN ® W 6.8% ATTACOTE ® LVM SELLOGEN ® W is a trademark product of Henkel Corporation and is an alkyl naphthalene sulfonate. ATTACOTE ® LVM is a trademark product of Engelhard Corporation and is an attapulgite clay. Chlorothalonil (tetrachloroisophthalonitrile) is manufactured by several companies and is sold, for example, as a 95-97% technical grade fungicide under the trade name DACONIL ® by ISK Biosciences. The following dispersants were used in the above formulation.
- the wetting time was evaluated for each wettable powder as follows. 5.0 grams of powder was quickly placed onto the surface of 100 mL of water (containing 500 ppm hardness) in a 250 mL beaker, distributing the powder over the surface as quickly and evenly as possible. A stop watch was used to measure the time required to completely wet the powder. Formulation Wetting time (seconds)
- the following procedure was used to measure attrition of the WDGs described herein. To a 100 mL round glass bottle was added 5 grams of WDG and 20 grams of 5-mm high-density alumina shot. The bottle was rotated on a Turbulator blender (Glen Mills Inc., Clifton, N.J.) for 2 minutes. The attrition is computed as the weight percent of the mechanical breakdown of the granules that passed through a U.S. Standard sieve with 400-micron apertures.
- Wettable powders were made as described in Example 4 except the dispersant was used at 12%, SELLOGEN® W was used at 3%, and 1% sodium sulfate was used in place of ATTACOTE® LVM.
- the wettable powders were converted into extruded WDGs by (1) spraying a fine mist of water onto the powder contained in a round quart jar while rotating the jar manually until the powder was transformed into a uniformly wet paste, (2) extruding the paste through a 0.8 mm screen to yield extruded granules that were typically 2-4 mm in length, and (3) drying the extrudate in a fluid bed dryer for about one hour at 45° C., which yielded granules containing 1-2% moisture.
- the dispersibility was measured by the number of complete inversions required to completely disperse 1.25 g of test material in 250 mL of water of standard hardness contained in a 250 mL graduated cylinder.
- the suspensibility was measured according to CIPAC MT 15.1 in water of standard hardness at 25+/ ⁇ 1° C.
- the term “paste” refers to the extrudable wet mixture that is obtained by spraying water onto a wettable powder.
- the percent moisture in this extrudable paste was determined by weighing the jar containing the wettable powder before and after the water additions, and then dividing the weight of the added water by the weight of the extrudable wet mixture and multiplying by 100%.
- the granular bulk density was determined as the apparent density of loosely packed material. Specifically, 10 grams of material was poured into a 100 mL graduated cylinder and the volume was measured. The bulk density in pounds per cubic foot was calculated as 624 divided by this measured volume.
- the granules exhibited
- a concentrated aqueous solution of sodium lignosulfonate (CAS 8061-51-6) sold by Westvaco under the tradename KRAFTSPERSE® EDF-750, a neutral pH dispersant/disintegrant based on a high degree of sulfonation, low molecular weight kraft lignin was blended with AGRIMUL® PG 2067 Surfactant. The pH of the solution was adjusted to about 7.0 by adding sulfuric acid. Then, this mixture was spray dried. After spray drying, the composite spray-dried dispersant contained (on a DRY weight basis) 85-90% sodium lignosulfonate and 10-15% alkyl polyglycoside. Thus, the alkyl polyglycoside to lignosulfonate ratio in this blend falls in the range from 1:9 ratio (10% alkyl polyglycoside) to a 15:85 ratio (15% alkyl polyglycoside).
- Example 3 The procedure of Example 3 was repeated wherein 11.1 Kg AGRIMUL® PG 2069 and 38.9 Kg REAX® 88B were used. However, this mixture was acidified to pH 4.5 by adding sulfuric acid. After spray drying, the composite spray-dried dispersant contained (on a DRY weight basis) about 75% sodium lignosulfonate and about 25% alkyl polyglycoside. The spray-dried solid was observed to flow freely and dissolved completely in water at 21° C.
Abstract
Description
R1O(R2O)b(Z)n I
wherein R1 is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6. Preferred alkyl polyglycosides which can be used in the compositions according to the invention have the formula I wherein Z is a glucose residue and b is zero. Such alkyl polyglycosides are commercially available, for example, as APG®, GLUCOPON®, PLANTAREN® or AGRIMUL® surfactants from Henkel Corporation, Ambler, Pa., 19002. Examples of such surfactants include but are not limited to:
- 1. GLUCOPON® 220 Surfactant—an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.5.
- 2. GLUCOPON® 225 Surfactant—an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
- 3. GLUCOPON® 600 Surfactant—an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- 4. GLUCOPON® 625 Surfactant—an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- 5. APGO 325 Surfactant—an alkyl polyglycoside in which the alkyl group contains 9 to 11 carbon atoms and having an average degree of polymerization of 1.6.
- 6. PLANTAREN® 2000 Surfactant—an alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- 7. PLANTAREN® 1300 Surfactant—an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
- 8. AGRIMUL® PG 2067 Surfactant—an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
- 9. AGRIMUL® PG 2076 Surfactant—an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.5.
Wt % | Component |
84.2% | Chlorothalonil (95%) |
8.0% | Dispersant (see table below) |
1.0% | SELLOGEN ® W |
6.8% | ATTACOTE ® LVM |
SELLOGEN ® W is a trademark product of Henkel Corporation and is an alkyl naphthalene sulfonate. | |
ATTACOTE ® LVM is a trademark product of Engelhard Corporation and is an attapulgite clay. | |
Chlorothalonil (tetrachloroisophthalonitrile) is manufactured by several companies and is sold, for example, as a 95-97% technical grade fungicide under the trade name DACONIL ® by ISK Biosciences. |
The following dispersants were used in the above formulation.
Formulation | Dispersant | ||
a | REAX ® 85A (as a 100% solid) | ||
b | solid from example 2 | ||
c | REAX ® 88B (as a 100% solid) | ||
d | solid from example 3 | ||
Formulation | Wetting time (seconds) | ||
a | 3420 | ||
b | 86 | ||
c | 1500 | ||
d | 57 | ||
TABLE 1 | |||
GRANULE | ATTRITION | ||
PASTE | (bulk | (% < 400 MICRONS) |
(% | density; | t = 1 month | ||
DISPERSANT | H2O) | lbs/ft3) | t = 0 | @ 54° C. |
LLS | 10.3 | 33.0 | 55 | 55 |
APS + LLS(liq) | 11.5 | 40.3 | 0 | 0.1 |
APS + LLS(dry) | 7.5 | 39.0 | 0.2 | 0.1 |
HLS | 15.9 | 44.0 | 2 | 5 |
APS + HLS(liq) | 14.6 | 48.0 | 0.5 | 0 |
APS + HLS(dry) | 10.6 | 44.6 | 5 | 5 |
MOREWET ® | 10.5 | 40.0 | 33 | 36 |
D-425 | ||||
KRAFTSPERSE ® | 12.5 | 37.0 | 28 | 12 |
EDF-350 | ||||
POLYFON ® F | 10.5 | 31.0 | 74 | 78 |
LLS = REAX ® 88B (a LS of lower MW) | ||||
HLS = REAX ® 85A (a LS of higher MW) | ||||
APS = AGRIMUL ® PG 2076 | ||||
APS + LLS(liq) - APS and LLS were added to the WDG premix as a liquid blend | ||||
APS + LLS(dry) - APS and LLS were added to the WDG premix as a spray-dried solid | ||||
APS + HLS(liq) - APS and HLS were added to the WDG premix as a liquid blend | ||||
APS + LLS(dry) - APS and LLS were added to the WDG premix as a spray-dried solid |
TABLE 2 | |||
DISPER- | SUSPEN- | SUSPEN- | |
SIBILITY | SIBILITY | SIBILITY | |
(342 PPM) | (342 PPM) | (1000 PPM) |
t = | t = | t = | ||||
1 month | 1 month | 1 month | ||||
DISPER- | @ | @ | @ | |||
SANT | t = 0 | 54° C. | t = 0 | 54° C. | t = 0 | 54° C. |
LLS | 11 | 12 | 82 | 81 | 80 | 80 |
APS + LLS(liq) | 11 | 12 | 84 | 83 | 83 | 81 |
APS + LLS(dry) | 8 | 8 | 81 | 72 | 78 | 80 |
HLS | 16 | 14 | 85 | 64 | 81 | 53 |
APS + HLS(liq) | 13 | 15 | 84 | 83 | 81 | 85 |
APS + HLS(dry) | 5 | 6 | 87 | 79 | 81 | 76 |
MOREWET ® | 16 | 14 | 63 | 68 | 51 | 65 |
D-425 | ||||||
KRAFTSPERSE ® | 7 | 8 | 80 | 78 | 79 | 76 |
EDF-350 | ||||||
POLYFON ® F | 5 | 3 | 90 | 85 | 85 | 46 |
LLS = REAX ® 88 (a LS of lower MW) | ||||||
HLS = REAX ® 85A (a LS of higher MW) | ||||||
APS = AGRIMUL ® PG 2076 | ||||||
APS + LLS(liq) - APS and LLS were added to the WDG premix as a liquid blend | ||||||
APS + LLS(dry) - APS and LLS were added to the WDG premix as a spray-dried solid | ||||||
APS + HLS(liq) - APS and HLS were added to the WDG premix as a liquid blend | ||||||
APS + LLS(dry) - APS and LLS were added to the WDG premix as a spray-dried solid |
S | SS | t = 0 | t = 1 | |
Disp (c) | ||||
4% | 3 | 9 | 96 | 20 |
6% | 3 | 7 | 94 | 51 |
8% | 3 | 5 | 97 | 73 |
10% | 3 | 3 | 97 | 95 |
12% | 3 | 1 | 99 | 96 |
16% | 0 | 0 | 99 | 97 |
Disp (d) | ||||
4% | 3 | 9 | 96 | 30 |
6% | 3 | 7 | 96 | 66 |
8% | 3 | 5 | 97 | 93 |
10% | 3 | 3 | 98 | 94 |
12% | 3 | 1 | 99 | 94 |
Disp (C) is APS + LLS(dry) | ||||
Disp (d) is APS + HLS(dry) |
Claims (20)
R1O(R2O)b(Z)a I
R 1O(R2O)b(Z)a I
R1(R2O)b(Z)a I
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/334,366 US6855327B1 (en) | 1998-07-02 | 1999-06-16 | Pesticide dispersant |
TR2000/01245T TR200001245T1 (en) | 1998-07-02 | 1999-07-02 | Spruce drug dispenser. |
CA002302949A CA2302949A1 (en) | 1998-07-02 | 1999-07-02 | Pesticide dispersant |
PCT/US1999/014127 WO2000001234A1 (en) | 1998-07-02 | 1999-07-02 | Pesticide dispersant |
BR9906827-3A BR9906827A (en) | 1998-07-02 | 1999-07-02 | Composite dispersing agent, composition, and, product of a process |
NZ503167A NZ503167A (en) | 1998-07-02 | 1999-07-02 | Pesticide dispersant having a composite dispersing agent containing an alkyl polyglycoside and a polymeric anionic dispersant |
AU48284/99A AU4828499A (en) | 1998-07-02 | 1999-07-02 | Pesticide dispersant |
EP99931866A EP1018872A4 (en) | 1998-07-02 | 1999-07-02 | Pesticide dispersant |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9163598P | 1998-07-02 | 1998-07-02 | |
US09/334,366 US6855327B1 (en) | 1998-07-02 | 1999-06-16 | Pesticide dispersant |
Publications (1)
Publication Number | Publication Date |
---|---|
US6855327B1 true US6855327B1 (en) | 2005-02-15 |
Family
ID=26784172
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/334,366 Expired - Lifetime US6855327B1 (en) | 1998-07-02 | 1999-06-16 | Pesticide dispersant |
Country Status (8)
Country | Link |
---|---|
US (1) | US6855327B1 (en) |
EP (1) | EP1018872A4 (en) |
AU (1) | AU4828499A (en) |
BR (1) | BR9906827A (en) |
CA (1) | CA2302949A1 (en) |
NZ (1) | NZ503167A (en) |
TR (1) | TR200001245T1 (en) |
WO (1) | WO2000001234A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060035787A1 (en) * | 2002-08-07 | 2006-02-16 | Hiroshi Dairiki | Agricultural chemical composition in granular form |
US20090072182A1 (en) * | 2007-09-19 | 2009-03-19 | Baum's Flame Management, Llc | Fire fighting and cooling composition |
WO2012166392A1 (en) | 2011-05-20 | 2012-12-06 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Paenibacillus alvei strain ts-15 and its use in controlling pathogenic organisms |
US8536095B2 (en) | 2008-07-03 | 2013-09-17 | Monsanto Technology Llc | Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants |
US20150196023A1 (en) * | 2009-04-22 | 2015-07-16 | Akzo Nobel Chemicals International B.V. | Dispersants for agricultural applications |
WO2016108929A1 (en) * | 2014-12-31 | 2016-07-07 | Dow Agrosciences Llc | Microencapsulated nitrification inhibitor compositions |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050009707A1 (en) * | 2003-07-02 | 2005-01-13 | Pompeo Michael P. | APG granulates containing agrochemical active ingredients |
BRPI0509858A (en) * | 2004-04-14 | 2007-10-09 | Fmc Corp | soluble granule composition, method for controlling unwanted pests, and process for preparing a soluble granule composition |
NZ564086A (en) * | 2005-06-02 | 2010-10-29 | Akzo Nobel Nv | Synergistic blends of (alkyl) naphthalene formaldehyde condensate sulfonates and lignosulfonates useful in agrochemical formulations |
ES2383820T3 (en) * | 2005-09-09 | 2012-06-26 | Bayer Cropscience Ag | Solid formulations of fungicide mixtures |
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1999
- 1999-06-16 US US09/334,366 patent/US6855327B1/en not_active Expired - Lifetime
- 1999-07-02 CA CA002302949A patent/CA2302949A1/en not_active Abandoned
- 1999-07-02 EP EP99931866A patent/EP1018872A4/en not_active Withdrawn
- 1999-07-02 TR TR2000/01245T patent/TR200001245T1/en unknown
- 1999-07-02 AU AU48284/99A patent/AU4828499A/en not_active Abandoned
- 1999-07-02 WO PCT/US1999/014127 patent/WO2000001234A1/en not_active Application Discontinuation
- 1999-07-02 NZ NZ503167A patent/NZ503167A/en unknown
- 1999-07-02 BR BR9906827-3A patent/BR9906827A/en not_active Application Discontinuation
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US4895622A (en) | 1988-11-09 | 1990-01-23 | Betz Laboratories, Inc. | Press felt conditioner for neutral and alkaline papermaking systems |
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060035787A1 (en) * | 2002-08-07 | 2006-02-16 | Hiroshi Dairiki | Agricultural chemical composition in granular form |
US8163674B2 (en) * | 2002-08-07 | 2012-04-24 | Nippon Soda Co., Ltd. | Agricultural chemical composition in granular form |
US20090072182A1 (en) * | 2007-09-19 | 2009-03-19 | Baum's Flame Management, Llc | Fire fighting and cooling composition |
US8536095B2 (en) | 2008-07-03 | 2013-09-17 | Monsanto Technology Llc | Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants |
US9351486B2 (en) | 2008-07-03 | 2016-05-31 | Monsanto Technology Llc | Combinations of derivatized saccharide surfactants and etheramine oxide surfactants as herbicide adjuvants |
US20150196023A1 (en) * | 2009-04-22 | 2015-07-16 | Akzo Nobel Chemicals International B.V. | Dispersants for agricultural applications |
US9526241B2 (en) * | 2009-04-22 | 2016-12-27 | Akzo Nobel Chemicals International B.V. | Dispersants for agricultural applications |
WO2012166392A1 (en) | 2011-05-20 | 2012-12-06 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Paenibacillus alvei strain ts-15 and its use in controlling pathogenic organisms |
WO2016108929A1 (en) * | 2014-12-31 | 2016-07-07 | Dow Agrosciences Llc | Microencapsulated nitrification inhibitor compositions |
Also Published As
Publication number | Publication date |
---|---|
EP1018872A4 (en) | 2000-10-11 |
TR200001245T1 (en) | 2000-11-21 |
EP1018872A1 (en) | 2000-07-19 |
NZ503167A (en) | 2001-09-28 |
BR9906827A (en) | 2000-08-15 |
WO2000001234A1 (en) | 2000-01-13 |
CA2302949A1 (en) | 2000-01-13 |
AU4828499A (en) | 2000-01-24 |
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